- Tetrazoles: XLV. Amidoalkylation of 5-Substituted Tetrazoles
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Amidoalkylation of 5-aryl(hetaryl)tetrazoles with N-hydroxymethylamides of aliphatic and aromatic carboxylic acids occurs regioselectively and yields mainly 5-aryl(hetaryl)-2-acylaminomethyltetrazoles. These compounds are fairly stable in neutral media bu
- Myznikov,Esikov,Artamonova,Koldobskii
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- Rectangular ZnO porous nano-plate assembly with excellent acetone sensing performance and catalytic activity
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The controlled synthesis of a hierarchically assembled porous rectangular ZnO plate (2.5-3.5 μm length, 1.5-2.5 μm width and 100-150 nm thickness) from bulk ZnO without using any organic substrates, such as solvents/surfactants/structure-directing agents, is presented. The synthesized ZnO plates are single crystalline with exposed (1010) facets on the flat surface, porous and formed through the calcination of a hydrozincite [Zn5(CO3)2(OH)6] intermediate. A gas sensor based on the synthesized porous ZnO architecture exhibited high sensitivity towards acetone even in low concentration (S = 3.4 in 1 ppm acetone) with good selectivity. The ZnO nanostructured material as a heterogeneous catalyst also showed excellent catalytic activity for the synthesis of 5-substituted-1H-tetrazoles (yield = 94%). Both the activities are superior than those of other reported ZnO based acetone sensors and heterogeneous catalysts. We believe that the improved properties of the synthesized ZnO nanostructure is due to the exposed (1010) facets, and its porous and assembled structure, which provides a reasonably large accessible surface area, and facilitates diffusion and mass transport of gas or substrate molecules.
- Giri, Arnab Kanti,Saha, Arka,Mondal, Aniruddha,Chandra Ghosh, Subhash,Kundu, Susmita,Panda, Asit Baran
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p. 102134 - 102142
(2015)
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- Tetrazoles: Calcium oxalate crystal growth modifiers
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Molecules containing tetrazole substituents have become of interest due to their being bioisosteres of carboxylic acids and like their carboxylate counterparts, tetrazolate anions have been able to affect the crystal growth of barium sulphate and calcium carbonate. In this proof of principle study, we show that this behaviour also extends to calcium oxalate and therefore opens the possibility of using tetrazole-based additives for investigating mineralization processes of human pathological relevance. This journal is
- McMulkin, Calum J.,Massi, Massimiliano,Jones, Franca
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- Self-healing and moldable material with the deformation recovery ability from self-assembled supramolecular metallogels
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A self-assembled non-covalent metallogel system with self-healing, deformation recoverable, moldable and bottom-up load-bearing properties was prepared using tetrazolyl derivatives and Pd(OAc)2. This journal is
- Yan, Liwei,Gou, Shaohua,Ye, Zhongbin,Zhang, Shihong,Ma, Lihua
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- Synthesis, characterization, and biological evaluation of oxadiazole derivatives bearing 5-phenyl-tetrazole as osteoclast differentiation inhibitors
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Novel oxadiazoles bearing 5-phenyl-tetrazole (5a-k) were designed and efficiently synthesized by treating 2-(5-phenyl-2H-tetrazole-2-yl)acetohydrazide (4) with aromatic carboxylic acids in POCl3, and their in vitro anti-osteoclastogenic activities were evaluated. In the cell-based osteoclast differentiation model, all compounds (5a-k) inhibited the formation of osteoclasts. In addition, the potential target molecules of compound 5 analogs were predicted with their chemical substructures via a web-based interface, and some of them were found to be related to osteoclast differentiation. Consequently, the scaffold containing oxadiazole-tetrazole in a single molecule and their analogs are of potential use in the design of novel anti-osteoclastogenic therapeutics.
- Moon, Seong-Hee,Latif, Muhammad,Qasim, Muhammad,Choi, Sik-Won,Lee, Joo Yun,Byun, Byung Jin,Saeed, Aamer,Kim, Seong Hwan
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- Non-catalyzed addition of heterocyclic thiols and 5-substituted-1H-tetrazoles to vinyl ethers
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The alkylation of 1-substituted 1H-tetrazole-5-thiols and 4-substituted 4 H-1,2,4-triazole-3-thiols with alkyl halides or sulfonates lead to the formation of S-alkylated products regardless of the substituent on the heterocycle. In this work, we found that substituted 1H-tetrazole-5-thiols and 4 H-1,2,4-triazole-3-thiols readily reacted with vinyl ethers in the absence of a catalyst to exclusively form N-substituted 1H-tetrazole-5(4H)-thiones and 1H-1,2,4-triazole-5(4H)-thiones, respectively. Furthermore, the reactions of 5-substituted-1H-tetrazoles with vinyl ethers under the same conditions selectively yielded 2,5-disubstitued tetrazoles.
- Melnikova, Iuliia,Roh, Jaroslav,Kune?, Ji?í,Artamonova, Tatiana,Zevatskii, Yuri,Myznikov, Leonid
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- Investigation of N-[(acyloxy)alkyl] ester as a prodrug model for drugs containing the phenyltetrazole moiety
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N-Acyloxyalkylation using 5-phenyltetrazole as a model compound was investigated as a general means of prodrug modification of the tetrazole ring with a view to change the physicochemical properties for improving biomembrane transport. Pivaloxymethylation
- Alexander,Renyer,Rork
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- A novel route for the synthesis of 5-substituted 1-: H tetrazoles in the presence of polymer-supported palladium nanoparticles
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A novel method for the synthesis of 5-substituted 1-H tetrazoles has been developed using one-pot tandem reactions of aryl halides with K4[Fe(CN)6] and sodium azide in the presence of cross-linked poly(4-vinylpyridine)-stabilized Pd(0) nanoparticles, [P4-VP]-PdNPs. The catalyst was characterized using various techniques such as FT-IR and UV-vis spectroscopy, AAS, TEM, FESEM, EDX analysis, XRD and XPS. The results confirm a good dispersion of palladium nanoparticles on the polymer support. The catalyst is reusable many times without a significant loss in its activity.
- Darbandizadeh Mohammad Abadi, Seyed Shahab Addin,Karimi Zarchi, Mohammad Ali
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- Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation
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An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37?:?63->99?:?1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.
- Xie, Ming-Sheng,Cheng, Xuan,Chen, Yang-Guang,Wu, Xiao-Xia,Qu, Gui-Rong,Guo, Hai-Ming
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- Dendron-functionalized Fe3O4 magnetic nanoparticles with palladium catalyzed CN insertion of arylhalide for the synthesis of tetrazoles and benzamide
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A novel method for the one-pot synthesis of 5-substituted 1H-tetrazoles and Benzamide from arylhalide containing in situ CN insertion from inorganic salt source was accomplished in presence of a new magnetically catalyst, palladium on surface-modified Schiff-Base complex. K2[Ni(CN)4] plays a role of nontoxic inorganic cyanide source in arylhalide Nucleophilic substitution. The synthesized Pd-Schiff-Base@Fe3O4MNPs was characterized by various techniques such as FT-IR, TGA, SEM, VSM, XRD, TEM, ICP-AES, EDX, BET and XPS. The nano structure catalyst was easily recovered by external magnetic field and reused several times without noticeable loss of its catalytic activity. Leaching study of Pd-Schiff-Base@Fe3O4 MNPs shows palladium strong bonded to different active parts of catalyst surface. Heterogeneity of this catalyst has been examined using hot filtration and ICP-AES techniques.
- Karimi Zarchi, Mohammad Ali,Darbandizadeh Mohammad Abadi, Seyed Shahab Addin
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- An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates
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A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide-oxygen for elimination and azide source. Various amides were converted into th
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
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- 1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1H-tetrazoles
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A simple, green and efficient method has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction in good to excellent yields between various benzonitriles and sodium azide. For this purpose, 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ([BiPy](HSO3)2Cl2) system as an ionic liquid catalyst have been extended for the construction of these valuable products. This procedure has significant advantages, including using ethylene glycol as a green solvent. The other advantages of this method are inexpensive and ease the preparation of the catalyst, mild reaction conditions, green reaction medium, easy workup, short reaction time, and simple experimental process.
- Aali, Elaheh,Gholizadeh, Mostafa,Noroozi-Shad, Nazanin
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- The mineral alum: an effective and low-cost heterogeneous catalyst for the successful synthesis of 5-substituted-1H-tetrazoles
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A simple, efficient, and green procedure for the synthesis of 5-substituted-1H-tetrazoles via [3 + 2] cycloaddition reaction of nitriles with sodium azide is described. The reaction was catalyzed by natural and mesoporous alum nanoparticles (NPs) in DMSO
- Karimian, Azam,Emarloo, Nahid,Salari, Samira
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- Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) Nanostructures
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Abstract: The synthesis of 5-substituted 1H-tetrazoles by use of a series of M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) nanocatalysts are presented. Following the optimized conditions, Co-SAPO-34 nanocatalyst has been found to effectively catalyze the 5-substi
- Baghershiroudi, Mahrokh,Bafandeh, Fereshteh Taghipour,Safa, Kazem D.,Panahi, Parvane Nakhostin
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p. 230 - 236
(2021/04/09)
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- Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles
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An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.
- Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
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- Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex
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A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.
- Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed
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- Magnetization of biochar nanoparticles as a novel support for fabrication of organo nickel as a selective, reusable and magnetic nanocatalyst in organic reactions
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Catalyst species are an important class of materials in chemistry, industry, medicine and biotechnology. Also, waste recycling is an important process in green chemistry and economic efficiency. Therefore, in order to recycle waste, biochar nanoparticles were prepared from chicken manure. Then, the biochar nanoparticles were magnetized under a green and environmentally friendly method. Finally, the surface of the magnetic biochar nanoparticles was modified and further they were applied as a novel support for fabrication of nickel as a homoselective and reusable catalyst in organic reactions. The structure of this organic-inorganic catalyst has been characterized by N2adsorption-desorption isotherms, and the SEM, EDS, WDX, XRD, TGA, AAS, FT-IR and VSM techniques. This magnetically recyclable catalyst was used in the homoselective synthesis of tetrazole and pyranopyrazole derivatives. This catalyst can be reused several times without significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst were studied by hot filtration and the AAS technique. Also, the reused catalyst was characterized by the SEM, EDS, AAS and BET techniques.
- Moradi, Parisa,Hajjami, Maryam
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p. 2981 - 2994
(2021/02/26)
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- An efficient Cu/functionalized graphene oxide catalyst for synthesis of 5-substituted 1H-tetrazoles
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The copper nanoparticles (Cu NPs) and amide functionalized graphene oxide (Cu-Amd-RGO) catalyst were prepared. This prepared catalyst (Cu-Amd-RGO) used for the synthesis of tetrazole derivatives. The catalyst (Cu-Amd-RGO) was characterized by field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction analysis (XRD). The average particle size of Cu was found to be 7.6?nm. The Cu-Amd-RGO catalyst exhibited excellent catalytic activity and recyclability for synthesis of tetrazoles.
- Kulkarni, Padmakar A.,Satpati, Ashis Kumar,Thandavarayan, Maiyalagan,Shendage, Suresh S.
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p. 2891 - 2899
(2021/02/12)
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- Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst
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Herein, catalytic application of a metal-free sulfonic acid functionalized reduced graphene oxide (SA-rGO) material is reported for the synthesis of both carboxylic acids and their bioisosteres, 5-substituted-1H-tetrazoles. SA-rGO as a catalytic material incorporates the intriguing properties of graphene oxide material with additional benefits of highly acidic sites due to sulfonic acid groups. The oxidation of aldehydes to carboxylic acids could be efficiently achieved using H2O2as a green oxidant with high TOF values (9.06-9.89 h?1). The 5-substituted-1H-tetrazoles could also be effectively synthesized with high TOF values (12.08-16.96 h?1). The synthesis of 5-substituted-1H-tetrazoles was corroborated by single crystal X-ray analysis and computational calculations of the proposed reaction mechanism which correlated well with experimental findings. Both of the reactions could be performed efficiently at gram scale (10 g) using the SA-rGO catalyst. SA-rGO displays eminent reusability up to eight runs without significant decrease in its productivity. Thus, these features make SA-rGO riveting from an industrial perspective.
- Mittal, Rupali,Kumar, Amit,Awasthi, Satish Kumar
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p. 11166 - 11176
(2021/03/31)
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- Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions
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Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]
- Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh
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p. 2420 - 2435
(2021/01/04)
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- Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands
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A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.
- Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
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- Coupling ofN-tosylhydrazones with tetrazoles: synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics
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Coupling reactions ofO-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-d-glycopyranosylmethyl-2H-tetrazoles in 7-67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies withC-(β-d-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-d-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.
- Kaszás, Tímea,Cservenyák, Ivett,Juhász-Tóth, éva,Kulcsár, Andrea E.,Granatino, Paola,Nilsson, Ulf J.,Somsák, László,Tóth, Marietta
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supporting information
p. 605 - 618
(2021/02/06)
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- Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates
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A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.
- Bagherzadeh, Nastaran,Sardarian, Ali Reza,Eslahi, Hassan
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- The anchoring of a Cu(ii)-salophen complex on magnetic mesoporous cellulose nanofibers: green synthesis and an investigation of its catalytic role in tetrazole reactions through a facile one-pot route
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Today, most synthetic methods are aimed at carrying out reactions under more efficient conditions and the realization of the twelve principles of green chemistry. Due to the importance and widespread applications of tetrazoles in various industries, especially in the field of pharmaceutical chemistry, and the expansion of the use of nanocatalysts in the preparation of valuable chemical reaction products, we decided to use an (Fe3O4@NFC@NSalophCu)CO2H nanocatalyst in this project. In this study, the synthesis of the nanocatalyst (Fe3O4@NFC@NSalophCu)CO2H was explained in a step-by-step manner. Confirmation of the structure was obtained based on FT-IR, EDX, FE-SEM, TEM, XRD, VSM, DLS, TGA, H-NMR, and CHNO analyses. The catalyst was applied to the synthesis of 5-substituted-1H-tetrazole and 1-substituted-1H-tetrazole derivatives through multi-component reactions (MCRs), and the performance was assessed. With advances in science and technology and increasing environmental pollution, the use of reagents and methods that are less dangerous for the environment has received much attention. Therefore, following green chemistry principles, with the help of the (Fe3O4@NFC@NSalophCu)CO2H salen complex as a nanocatalyst that is recyclable, cheap, safe, and available, the use of water as a green solvent, and reduced reaction times, the synthesis of tetrazoles can be achieved.
- Bagherzade, Ghodsieh,Ghamari kargar, Pouya
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p. 19203 - 19220
(2021/06/03)
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- Magnetic nitrogen-doped carbon derived from silk cocoon biomass: a promising and sustainable support for copper
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In this study, a magnetic nitrogen-doped carbon-based copper (MNC-Cu) catalyst was fabricated so that natural silk cocoons undergo thermal processes and then activate by combining with Fe3O4 MNPs as a suitable substrate for placement copper metal. The efficiency of the generated catalyst in the synthesis of 5-substituted 1H-tetrazole derivatives was evaluated by the [3 + 2] cycloaddition reaction of aromatic aldehydes, azide ions, and hydroxylamines. FT-IR, FE-SEM, EDS, TEM, XRD, TGA, and VSM techniques have been adopted to identify and validate this heterogeneous catalyst. The observation from EDS, elemental mapping, XRD, and FT-IR analysis confirms the immobilization of Cu metals on the MNC surface and uniform distribution of species and then no aggregation occurs during functionalization. VSM results show the magnetic feature of fabricated catalyst, and based on the leaching test, the amount of catalyst leaching was negligible. Moreover, this reaction is a one-pot multicomponent reaction (MCRs) or more precisely a one-pot, three-component reaction, which is one of the advantages of this work. The fabricated catalyst shows high efficiency, good stability, and considerable reactivity in synthesizing 5-substituted 1H-tetrazole derivatives. So it can be seen that the fabricated magnetic catalyst is a useful and practical catalyst for synthesizing [3 + 2] cycloaddition reactions. Reusability and recyclability for five sequential runs without notable increase and reduction in activity are other advantages. In addition, the magnetic properties of this heterogeneous catalyst led to easy and quickly recovered and striking copper leaching. Graphical abstract: [Figure not available: see fulltext.]
- Akbarzadeh, Parisa,Koukabi, Nadiya,Tahmasbi, Marzieh
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- Methionine-Coated Fe3O4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles
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Abstract: Methionine-coated Fe3O4 nanoparticles, a magnetically reusable and environmentally friendly heterogeneous catalyst, was synthesized. The new catalyst was characterized by FT-IR spectra, XRD, SEM, and EDX analysis and was us
- Abbasi, R.,Karimian, A.,Namvar-Mhaboub, M.
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p. 1646 - 1653
(2020/10/22)
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- TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis
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Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 °C in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.
- Yoneyama, Hiroki,Oka, Naoki,Usami, Yoshihide,Harusawa, Shinya
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supporting information
(2020/01/21)
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- Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents
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Biochar is a carbon-rich solid which its surface was covered by high density of carbonyl, hydroxyl and carboxylic acid functional groups. In this work, biochar nanoparticles were prepared from pyrolysis of chicken manure and further a new copper catalyst
- Moradi, Parisa,Hajjami, Maryam,Tahmasbi, Bahman
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- Copper coordinated-poly(α-amino acid) decorated on magnetite graphene oxide as an efficient heterogeneous magnetically recoverable catalyst for the selective synthesis of 5- and 1-substituted tetrazoles from various sources: A comparative study
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In this work, poly(α-amino acid)-Cu(II) complex immobilized on magnetite graphene oxide (GO/Fe3O4?PAA-Cu-complex) was prepared via a multistep synthesis and employed as an efficient, heterogeneous, magnetically recyclable nanocatalyst for one-pot, three component synthesis of 5- and 1-substituted tetrazoles using different substrates including benzaldehydes, benzonitriles, and anilines in mild conditions. The different approaches were mechanically investigated and compared. The catalyst was fully characterized by Fourier transform infrared (FTIR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), energy dispersive X-ray spectroscopy (EDX), inductively coupled plasma (ICP), FE-SEM and TEM analyses. The magnetic nanocatalyst could be readily separated from the reaction mixture by an external magnet and reused for several times without significant loss of catalytic activity. Also, the spectroscopic analysis revealed the stability and durability of the catalyst. Finally, the chemoselectivity of the method was investigated by the various combinations of aldehyde, nitrile, and oxime.
- Kazemnejadi, Milad,Mahmoudi, Boshra,Sharafi, Zeinab,Nasseri, Mohammad A.,Allahresani, Ali,Esmaeilpour, Mohsen
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- Copper-based catalysts derived from salen-type ligands: Synthesis of 5-substituted-1: H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions
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Base-metal copper(ii) complexes derived from unsymmetrical salen-type ligands were designed and synthesized using ligands L1H to L4H in moderate yield. The synthesized unsymmetrical ligands L1H to L4H and the corresponding copper complexes (1-4) were characterized by UV-visible, IR and ESI-MS spectroscopic studies. Molecular structures of complexes 1, 2 and 4 were determined by X-ray crystallography. Copper complexes 1-4 were employed as catalysts for [3+2] cycloaddition and A3-coupling reactions. The mutual approach of salen-type ligands and metals via active participation of ligands allow to achieve the catalytic reactions. Reaction pathways were proposed and possible intermediate species during the catalytic cycle were successfully characterized by ESI-MS spectroscopic studies. This journal is
- Singh, Anshu,Maji, Ankur,Mohanty, Aurobinda,Ghosh, Kaushik
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p. 18399 - 18418
(2020/11/13)
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- Novel Hybrid Thioamide Ligand Supported Copper Nanoparticles on SBA-15: A Copper Rich Robust Nanoreactor for Green Synthesis of Triazoles and Tetrazoles in Water Medium
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Abstract: In this work, a new thioamide based ligand with reductive nature was designed for modification of mesoporous SBA-15. For this purpose, the channels of SBA-15 were modified with Tris(2-aminoethyl)amine (TAEA) groups and then reacted with S8 and phenyl acetylene to form thioamide groups via Willgerodt-Kindler reaction. This porous material proved to be an effective host for the immobilization of inexpensive Cu(II) ions. The catalytically active Cu(I) species were generated automatically due to the reductive nature of thioamide modified surface of catalyst without use of any toxic reducing agents. The well stabilized Cu(I) species into the nano-channels of SBA-15 were used for synthesis of various triazoles from sodium azide, phenyl acetylene and alkyl/benzyl halides or alkyl epoxides and various tetrazoles from sodium azide and aryl/alkyl nitriles under green mild aqueous reaction conditions. This catalytic system was used for 9 and 11 consecutive runs for synthesis of triazoles and tetrazoles, respectively. Graphic Abstract: [Figure not available: see fulltext.]
- Pourhassan, Fatemeh,Eshghi, Hossein
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p. 1287 - 1300
(2019/11/21)
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- Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst
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Nickel-anchored curcumin-functionalized boehmite nanoparticles (BNPs@Cur-Ni) as a robust and versatile nanocatalyst was synthesized and well-characterized by using Fourier transform infrared (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), X-ray mapping, thermogravimetric analysis (TGA), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), X-ray diffraction (XRD), and inductively coupled plasma optical emission spectroscopy (ICP-OES). The synthesis of 5-substituted 1H-tetrazoles and the oxidation of sulfides were conducted by BNPs@Cur-Ni with excellent turnover number (TON) and turnover frequency (TOF) outcomes. Also, the catalyst was reused for several sequential runs without Ni leaching or decreasing in reaction yield. Utilizing the curcumin and boehmite with a natural source as well as poly(ethylene glycol) (PEG) as a solvent in this simple protocol can be based on green chemistry rules.
- Jani, Muhammed Ali,Bahrami, Kiumars
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- Copper and nickel immobilized on cytosine@MCM-41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles
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In this work, a green approach is reported for efficient synthesis of biologically active tetrazole and pyranopyrazole derivatives in the presence of Cu-Cytosine@MCM-41 and Ni-Cytosine@MCM-41 (copper (II) and nickel (II) catalyst on the modified MCM-41 us
- Nikoorazm, Mohsen,Tahmasbi, Bahman,Gholami, Shahab,Moradi, Parisa
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- A robust and recyclable ionic liquid-supported copper(II) catalyst for the synthesis of 5-substituted-1H-tetrazoles using microwave irradiation
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Abstract: A novel and robust ionic liquid-supported copper(II) catalyst has been developed and explored for the efficient synthesis of 5-substituted-1H-tetrazoles using microwave irradiation. The ionic liquid-supported catalyst facilitated the efficient isolation of tetrazole products with high purity by simple extraction with organic solvent. Recovered ionic liquid-supported copper(II) catalyst could be recycled for three times for the synthesis of tetrazole products with high purity. This synthetic protocol offers a very clean, convenient, and microwave-assisted environment-friendly method for the efficient synthesis of 5-substituted-1H-tetrazoles with high yield. Graphic abstract: [Figure not available: see fulltext.].
- Padmaja,Chanda, Kaushik
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p. 1307 - 1317
(2019/11/14)
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- Palladium fabricated on boehmite as an organic-inorganic hybrid nanocatalyst for C-C cross coupling and homoselective cycloaddition reactions
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Herein, boehmite nanoparticles were prepared using an aqueous solution of NaOH and Al(NO3)3?9H2O at room temperature. After modification of the boehmite nanoparticle (BNP) surface by 3-choloropropyltrimtoxysilane (CPTMS), adenine was anchored on the surface. Finally, a complex of palladium was fabricated on the BNP surface (Pd-adenine@boehmite). The obtained nanoparticles were identified by TGA, FT-IR, BET, EDS, WDX, SEM, XRD and AAS techniques. In continuation, the Pd-adenine@boehmite was employed as an efficient, reusable and organic-inorganic hybrid catalyst in the C-C cross coupling reactions without a phosphine ligand or an inert atmosphere. Moreover, the homoselective synthesis of tetrazoles was studied in the presence of Pd-adenine@boehmite as a heterogeneous and practical nanocatalyst which can be recovered and reused in the described organic reactions. Besides, organic products which were isolated in suitable TOF and TON numbers in the presence of Pd-adenine@boehmite as a catalyst revealed the practicality of this catalyst. The heterogeneous nature of this catalyst was confirmed by TEM, EDS, WDX, AAS, and FT-IR techniques and, then, compared to the fresh catalyst.
- Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash,Moradi, Parisa
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p. 3717 - 3727
(2020/03/17)
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- Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane-Cu(I): a novel, highly efficient and reusable nanocatalyst for the C-C bond formation and the synthesis of 5-substituted 1H-tetrazoles in green media
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In this work, a versatile protocol was introduced for the preparation of a new Cu(I) supported complex on Silica supported boehmite nanoparticles (Boehmite@SiO2@Tris-Cu(I)). The structure of the catalyst was comprehensively characterized using
- Ghorbani-Choghamarani, Arash,Aghavandi, Hamid,Mohammadi, Masoud
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- Guanidine complex of copper supported on boehmite nanoparticles as practical, recyclable, chemo and homoselective organic–inorganic hybrid nanocatalyst for organic reactions
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Boehmite (BO) nanoparticles (NPs) were prepared via the injection of aqueous NaOH solution to aqueous aluminum nitrate solution at room temperature. Afterwards, a new complex of copper was immobilized on BO-NPs (Cu-Guanidine@BO-NPs). This heterogeneous nanocatalyst was used as a practical, recyclable, chemo and homoselective nanocatalyst in the organic processes, i.e. the preparation of tetrazole five-membered heterocycles and chemoselective sulfoxidation of sulfides using H2O2 as oxidant. In this sense, the prepared nanocatalyst was characterized by AAS, N2 adsorption–desorption isotherms, WDX, EDS, SEM, and TGA techniques. The reusability of this catalyst was investigated in the described organic reactions for several runs without notable loss of its catalytic activity. Moreover, all of the tetrazole and sulfoxide derivatives were isolated in high Turn Over Number (TON) and Turn Over Frequency (TOF) numbers indicating the high activity and selectivity of Cu-Guanidine@BO-NPs in the described reactions.
- Jafari, Fariba,Ghorbani-Choghamarani, Arash,Hasanzadeh, Neda
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- Ruthenium-Catalyzed meta-Selective C?H Nitration of Biologically Important Aryltetrazoles
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The first example of tetrazole-directed meta-selective C?H nitration is described. This transformation provided a straightforward approach for the synthesis of biologically important m-nitroaryltetrazoles in moderate to excellent yields with good functional group compatibility. In addition, new metallo-β-lactamase inhibitors were obtained by further transformation of the synthesized m-nitroaryltetrazoles. (Figure presented.).
- Chen, Jian,Huang, Tianle,Gong, Xinrui,Yu, Zhu-Jun,Shi, Yuesen,Yan, Yu-Hang,Zheng, Yang,Liu, Xuexin,Li, Guo-Bo,Wu, Yong
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supporting information
p. 2984 - 2989
(2020/06/08)
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- Discovery of mercaptopropanamide-substituted aryl tetrazoles as new broad-spectrum metallo-β-lactamase inhibitors
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β-Lactam antibiotic resistance mediated by metallo-β-lactamases (MBL) has threatened global public health. There are currently no available inhibitors of MBLs for clinical use. We previously reported the ruthenium-catalyzed meta-selective C-H nitration synthesis method, leading to some meta-mercaptopropanamide substituted aryl tetrazoles as new potent MBL inhibitors. Here, we described the structure-activity relationship of meta- and ortho-mercaptopropanamide substituted aryl tetrazoles with clinically relevant MBLs. The resulting most potent compound 13a showed IC50 values of 0.044 μM, 0.396 μM and 0.71 μM against VIM-2, NDM-1 and IMP-1 MBL, respectively. Crystallographic analysis revealed that 13a chelated to active site zinc ions via the thiol group and interacted with the catalytically important residues Asn233 and Tyr67, providing further structural information for the development of thiol based MBL inhibitors. This journal is
- Yan, Yu-Hang,Chen, Jian,Zhan, Zhen,Yu, Zhu-Jun,Li, Gen,Guo, Li,Li, Guo-Bo,Wu, Yong,Zheng, Yongxiang
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p. 31377 - 31384
(2020/09/21)
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- One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
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2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
- Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
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p. 7413 - 7423
(2020/07/07)
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- Synthesis and Photochemical Properties of Manganese(I) Tricarbonyl Diimine Complexes Bound to Tetrazolato Ligands
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Ten manganese(I) tricarbonyl diimine complexes bound to variably functionalised 5-aryl-tetrazolato ligands were prepared, and their photochemical properties were investigated. Upon exposure to light at 365 nm, each complex decomposed to its free diimine and tetrazolato ligands, simultaneously dissociating three CO ligands, as evidenced by changes in the IR spectra of the irradiated complexes over time. The anti-bacterial properties of one of these complexes were tested against Escherichia coli. While the complex displayed no effect on the bacterial growth in the dark, pre-irradiated solutions inhibited bacterial growth. Comparative studies revealed that the antibacterial properties originate from the presence of free 1,10-phenanthroline.
- Stout, Matthew J.,Stefan, Alessandra,Skelton, Brian W.,Sobolev, Alexandre N.,Massi, Massimiliano,Hochkoeppler, Alejandro,Stagni, Stefano,Simpson, Peter V.
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supporting information
p. 292 - 298
(2020/01/25)
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- Anchoring of Cu (II)-Schiff base complex on magnetic mesoporous silica nanoparticles: catalytic efficacy in one-pot synthesis of 5-substituted-1H-tetrazoles, antibacterial activity evaluation and immobilization of α-amylase
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Magnetic mesoporous silica nanocomposite, Fe3O4?MCM-41, was prepared and functionalized with N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (AEAPS). Then Schiff base grafted nanoparticles were synthesized by the condensation of 5,5'-
- Ahmadi, Ameneh,Azadi, Roya,Motamedi, Hossein,Sedaghat, Tahereh
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- Highly active and reusable cu/c catalyst for synthesis of 5-substituted 1h-tetrazoles starting from aromatic aldehydes
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A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddit
- Khalifeh, Reza,Khalili, Dariush,Rastegar, Najme
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p. 1044 - 1052
(2021/06/07)
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- Biosynthesis of Pd/MnO2 nanocomposite using Solanum melongena plant extract and its application for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides
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In this work, for the first time, Solanum melongena plant extract was used for the green synthesis of Pd/MnO2 nanocomposite via reduction osf Pd(II) ions to Pd(0) and their immobilization on the surface of manganese dioxide (MnO2) nanoparticles (NPs) as an effective support. The synthesized nanocomposite were characterized by various analytical techniques such as Fourier transform infrared (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), energy dispersive X-ray spectroscopy (EDS) and UV–Vis spectroscopy. The catalytic activity of Pd/MnO2 nanocomposite was used as a heterogeneous catalyst for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides containing various electron-donating or electron-withdrawing groups in the presence of K4[Fe (CN)6] as non-toxic cyanide source and sodium azide. The products were obtained in good yields via a simple methodology and easy work-up. The nanocatalyst can be recycled and reused several times with no remarkable loss of activity.
- Nasrollahzadeh, Mahmoud,Ghorbannezhad, Fatemeh,Sajadi, S. Mohammad
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- Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
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The preparation of 5-substituted 1H-tetrazoles was efficiently achieved by reaction of trimethylsilylazide with nitriles using a triorganotin alkoxide precatalyst. The reaction mechanism was first investigated using a homogeneous tributyltin derivative and was explored through experimental investigations and DFT calculations. A heterogeneous version was then developed using a polymer-supported organotin alkoxide and afforded an efficient method for the preparation of tetrazoles in high yields with an easy work-up and a residual tin concentration in the desired products compatible for pharmaceutical applications (less than 10 ppm). (Figure presented.).
- Chrétien, Jean-Mathieu,Kerric, Gaelle,Zammattio, Fran?oise,Galland, Nicolas,Paris, Michael,Quintard, Jean-Paul,Le Grognec, Erwan
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supporting information
p. 747 - 757
(2019/01/04)
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- Catalytic Synthesis of 5-Substituted Tetrazoles: Unexpected Reactions and Products
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Tetrazoles are incredibly useful organic molecules with a wide range of applications from medicinal chemistry as carboxylic acid isosteres to high energy density materials in space research. In an effort to develop an easy protocol for the synthesis of te
- Wani, Mohmmad Y.,Silva, Manuela R.,Krishnakumar, Balu,Kumar, Santosh,Al-Bogami, Abdullah S.,Aqlan, Faisal M.,Sobral, Abilio J. F. N.
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p. 1613 - 1621
(2019/04/26)
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- Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
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The metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin-iron (III) chloride (FeTSPP) was new employed in an environmentally benign protocol as an efficient catalyst for a “click” chemistry approach for the synthesis of tetrazole and guanindinyltetrazole derivatives via [2?+?3] cycloaddition reaction of nitriles and azide derivatives in aqueous medium. The synthesized compounds were obtained in excellent yield, short reaction times and a recoverable catalyst.
- El-Remaily, Mahmoud Abd El Aleem Ali Ali,Elhady
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- Ordered mesoporous SBA-15 functionalized with yttrium(III) and cerium(III) complexes: Towards active heterogeneous catalysts for oxidation of sulfides and preparation of 5-substituted 1H-tetrazoles
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Mesoporous SBA-15 was synthesized and modified with 3-chloropropyltrimethoxysilane and then used in immobilization of creatinine groups, which were employed to introduce Y3+ and Ce3+ to give rise to two novel yttrium and cerium catalysts: SBA-15@Creatinine@M (M?=?Y and Ce). The structures of the SBA-15@Creatinine@M catalysts were determined using various techniques. These catalysts offered outstanding catalytic performances in the oxidation of sulfides to sulfoxides and in the preparation of 5-substituted 1H-tetrazoles. An important characteristic of the SBA-15@Creatinine@M catalysts is that they are very stable without a considerable decrease in their catalytic performance lasting seven cycles.
- Molaei, Somayeh,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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- Immobilization of cerium (IV) and erbium (III) in mesoporous MCM-41: Two novel and highly active heterogeneous catalysts for the synthesis of 5-substituted tetrazoles, and chemo- and homoselective oxidation of sulfides
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Two well-ordered 2D-hexagonal cerium (IV) and erbium (III) embedded functionalized mesoporous MCM-41(MCM-41@Serine/Ce and MCM-41@Serine/Er) have been developed via functionalization of mesoporous MCM-41. The surface modification method has been used in the preparation of serine-grafted MCM-41 and led to the development of MCM-41@Serine. The reaction of MCM-41@Serine with Ce (NH4)2(NO3)6·2H2O or ErCl3·6H2O in ethanol under reflux led to the organization of MCM-41@Serine/Ce and MCM-41@Serine/Er catalysts. The structures of these catalysts were determined using scanning electron microscopy, mapping, energy-dispersive X-ray spectroscopy, Fourier transform-infrared, thermogravimetric analysis, X-ray diffraction, inductively coupled plasma, and Brunauer–Emmett–Teller analysis. These MCM-41@Serine/Ce and MCM-41@Serine/Er catalysts show outstanding catalytic performance in sulfides oxidation and synthesis of 5-substituted tetrazoles. These catalysts can be recycled for seven repeated reaction runs without showing a considerable decrease in catalytic performance.
- Molaei, Somayeh,Ghadermazi, Mohammad
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- Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid
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Fe3O4@SiO2–APTES-supported trifluoroacetic acid nanocatalyst was used for the one-pot synthesis of α-aminonitriles via a three-component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05?g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good-to-excellent yields in a short reaction time of 4?h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.
- Fatahi, Hosna,Jafarzadeh, Mohammad,Pourmanouchehri, Zahra
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p. 2090 - 2098
(2019/07/05)
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- Core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C) as a highly efficient and recoverable nanocatalyst for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides
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Fe3O4 magnetic nanoparticles were used as a core for Cu(II) Schiff base complex functionalized mesoporous MCM-41 shell to provide a core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C). A simple, environmentally friendly, inexpensive, green reaction conditions and efficient procedure for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides derivatives using this core–shell nanostructure as an efficient, novel and recoverable nanocatalyst has been described. Fe3O4?MCM-41?Cu-P2C is stable, cost-effective, heterogeneous, easy to handle and recoverable nanocatalyst and can be reused for several consecutive runs without a significant loss of catalytic activity. The catalyst was characterized by fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), powder X-ray diffractometer (XRD), scanning electron microscopy (SEM), atomic absorption spectroscopy (AAS), Brunauer–Emmett–Teller (BET) and vibrating sample magnetometer (VSM) techniques.
- Nikoorazm, Mohsen,Erfani, Zahra
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- Immobilization of Pd(0) complex on the surface of SBA-15: A reusable catalyst for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides
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A simple and efficient method for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides in the presence of Pd(0) complex immobilized on mesoporous SBA-15 as an efficient, recoverable and thermally stable mesostructure has been reported. Also, the prepared mesostructure was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray mapping, energy-dispersive X-ray spectroscopy, N2 adsorption and desorption, inductively coupled plasma optical emission spectroscopy and thermal gravimetric analysis. Then, this mesostructured catalyst was applied in the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides. The approach described here offers advantages such as short reaction times, high yield, purity yields, simple and eco- friendly, easy work-up. More importantly, this nanohybrid robust catalyst did not undergo metal leaching and applied several times without any decrease in catalytic activity.
- Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
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p. 374 - 380
(2018/11/01)
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- Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators
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The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.
- Sharma, Swagat,Kozek, Krystian A.,Abney, Kristopher K.,Kumar, Sushil,Gautam, Nagsen,Alnouti, Yazen,David Weaver,Hopkins, Corey R.
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p. 791 - 796
(2019/02/06)
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- Novel Benzohydroxamate-Based Potent and Selective Histone Deacetylase 6 (HDAC6) Inhibitors Bearing a Pentaheterocyclic Scaffold: Design, Synthesis, and Biological Evaluation
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Histone deacetylase 6 (HDAC6) is a peculiar HDAC isoform whose expression and functional alterations have been correlated with a variety of pathologies such as autoimmune disorders, neurodegenerative diseases, and cancer. It is primarily a cytoplasmic protein, and its deacetylase activity is focused mainly on nonhistone substrates such as tubulin, heat shock protein (HSP)90, Foxp3, and cortactin, to name a few. Selective inhibition of HDAC6 does not show cytotoxic effects in healthy cells, normally associated with the inhibition of Class I HDAC isoforms. Here, we describe the design and synthesis of a new class of potent and selective HDAC6 inhibitors that bear a pentaheterocyclic central core. These compounds show a remarkably low toxicity both in vitro and in vivo and are able to increase the function of regulatory T cells (Tregs) at well-tolerated concentrations, suggesting a potential clinical use for the treatment of degenerative, autoimmune diseases and for organ transplantation.
- Vergani, Barbara,Sandrone, Giovanni,Marchini, Mattia,Ripamonti, Chiara,Cellupica, Edoardo,Galbiati, Elisabetta,Caprini, Gianluca,Pavich, Gianfranco,Porro, Giulia,Rocchio, Ilaria,Lattanzio, Maria,Pezzuto, Marcello,Skorupska, Malgorzata,Cordella, Paola,Pagani, Paolo,Pozzi, Pietro,Pomarico, Roberta,Modena, Daniela,Leoni, Flavio,Perego, Raffaella,Fossati, Gianluca,Steinkühler, Christian,Stevenazzi, Andrea
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p. 10711 - 10739
(2019/12/02)
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- Cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf?-catalyzed one-pot three-component syntheses of 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in water
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The cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf? is easy to prepare and stable in air. The catalytic activity of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? as a neutral organotin Lewis acid catalyst is probed through the one-pot three-component syntheses of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine hydrochloride and sodium azide, and of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate. The reactions proceed well in the presence of 1?mol% of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? in water and provide the corresponding 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in good to excellent yields. The method reported has several advantages such as the catalyst being neutral, low catalyst loading and use of water as a green solvent.
- Wang, Hongshe,Zhao, Weixing,Du, Juan,Wei, Fenyan,Chen, Qi,Wang, Xiaomei
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- A Facile Approach to Catalyst-Free Cyanation and Azidation of a-Organic Compounds and a One-Pot Preparation of 5-Substituted 1 H-Tetrazoles by Using a Dimethyl Sulfoxide-Nitric Acid Combination
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In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ 4-sulfanecarbonitrile or azido(dimethyl)-λ 4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide-nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1 H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.
- Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Mahmoudi, Boshra,Nasseri, Mohammad Ali
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supporting information
p. 2290 - 2294
(2019/12/11)
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- Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1: H -tetrazoles in water
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Humic acid is a non toxic, inexpensive, easily available high-molecular weight polymer. A simple and facile one pot three-component synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxyamine hydrochloride and sodium azide using humic acid as an efficient catalyst in water is described. The method reported has several advantages such as high to excellent yields, easy work-up, mild reaction conditions, use of water as a green solvent, and a commercially available, nontoxic and reusable catalyst.
- Wang, Hongshe,Wang, Yichun,Han, Yinfeng,Zhao, Weixing,Wang, Xiaomei
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p. 784 - 789
(2020/01/23)
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- A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent
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A series of 5-substituted-1H-tetrazoles have been efficiently synthesized in moderate to excellent yields (68–90%) under mild reaction conditions by combining aryl aldehydes, hydroxylamine hydrochloride with sodium azide in the presence of catalytic amoun
- Xiong, Xingquan,Yi, Chao,Liao, Xu,Lai, Shilin
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p. 402 - 406
(2019/01/05)
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- Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies
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Benzoylhydrazine based Schiff base-ligated two new copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized by the reaction of Cu(CH3COO)2·H2O with respective Schiff base ligand 1-[(4-nitrophenyl)ethylidene] benzohydrazide (HL1) or 1-[(4-methoxyphenyl)ethylidene] benzohydrazide (HL2). Both complexes were isolated as greenish solid and fully characterized by elemental analysis, FT-IR, EPR, thermo-gravimetric (TG) analysis and Cyclic Voltammetry. The molecular structures of both complexes have also been determined by single crystal X-ray crystallography, which confirmed the coordination of Schiff base ligands through N, O donor atoms and distorted square planar geometry around the Cu(II) ion. Both complexes were found to be good homogeneous catalysts for the synthesis of a wide range of substituted thioethers and 5-substituted 1H-tetrazoles in 92% and 93% yield, respectively, at a low catalyst loading (0.5 mol%). The bond angles and distances, as discerned from the DFT calculations, commusurated with the experimental findings. The energy difference between the HOMO and the LUMO, calculated from DFT studies, was found to be 5.645 eV and 6.459 eV for complex 1 and complex 2, respectively. These results are in harmony with the observed higher catalytic activity of complex 1.
- Layek, Samaresh,Agrahari, Bhumika,Dey, Shuvankar,Ganguly, Rakesh,Pathak, Devendra D.
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p. 194 - 206
(2019/06/24)
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